Sam's sexual Pleasures
by romancelover42
Summary: Torturing Sam with sexual pleasure for hours with just slow fingering/tickle torture/toys etc
1. Chapter 1

Sam's Days of Sexual Pleasure

Dean and John had started torturing Sam with pleasure at the age of ten as they teased him with their fingers relentlessly fucking him, vibrators and dildos for hours a day with cock rings, and cock cages.

Then Dean had discovered something, and that was that Sam had a tickle fetish, he was turned on by being restrained and tickled agonizingly for hours.

So one morning Dean had a wicked idea for his little brother.

He woke Sam up in the bed by moving his hand that's draped over Sam up his brother's back making the shirt ride up and began dancing and ghosting his fingers lightly across his abdomen.

Back and forth he slowly dragged his fingers, and teased them slowly up Sam's chest and back down across his sides.

Hearing Sam moan he grinned up at his father as he pushed Sam's legs apart, and with teasing fingers slipped a cock cage on him, so no matter how aroused he became, he would not be able to orgasm until they gave him permission.

And it was about to be a very long few torturous days for Sam.

Lifting Sam's arm up slightly Dean could hear Sam waking more to their touches, as he slowly removed Sam's shirt and boxers, softly teasing with a stroking finger under Sam's armpit.

Sam moaned again and his eyes began flickering and Dean whispered in his ear with a grin, "Wake up little Sammy daddy and I've got a surprise for you. Come on Sammy."

Watching Sam's eyes open a bit he gently began tying Sam's wrists to the headboard, and his ankles outward so he was spread eagle on the bed.

Dean sits on the side of the bed and takes in the sight before him.

Once making sure the boy was thoroughly restrained that he couldn't get away, they admired the naked restrained young boy before them, so the thought that they were fully dressed made it further arousing.

John lightly began stroking the soles of Sam's ticklish feet.

Dean came around and slowly teasingly brushed Sam's ticklish neck at the same time.

Sam moaned and giggled slightly making both men grin at the young man's helplessness.

John wiggles all his fingers on Sam's feet slowly and agonizingly as Sam squirms trying to break away but there's no hope.

"Does this tickle Sammy?" Dean taunted.

All Sam could do was lay there and take it, laughing uncontrollably, and feeling himself getting hard at their soft touches.

"Oh Sammy Sammy Sammy." Dean comes to the side and lightly begins tickling both sides of his throat at the same time, dragging out the sensation, then down and back up his sides.

Sam can't help the huffing laughs that are being forced out of him.

He's so screwed.

His body has to struggle, has to try and get away and he alternates between jerking his legs up and down and then, as the panic escalates and the laughing threatens to bubble over completely, lifting his hips and straining right up off the chair.

Dean's fingers wiggle stroke and scratch softly all around his tummy, sides, and even his nipples beginning to grow hard, and it makes Sam a little crazy.

Sam's poor body is so confused.

Fighting his ropes is making it very clear that he's helplessly at his father and brother's mercy.

He doesn't want to have a hard on for being systematically taken apart by his big brother and father but there's not a damn thing he can do about it and God, that's only making him harder.

He thrashes and strains but the laughter is getting louder and his struggles weaker.

He's never seen Dean or his father looking so pleased.

"No! Stop! Dean! Naaghahahahaha!"

There's no way either of them are stopping because this is way too good.

Sam's laughter was barking, almost painful at first, but now it's coming easy and constant, rolling out like he can't stop, and he can't because they're not letting him.

Sam feels his smile, huge and dimpled.

His face is hot with exertion and John's looking at him as though he's a cute puppy.

John concentrates on one foot and then the other.

Sam pumps his hips with that big tent in his shorts and he knows it's lewd but he's not in control.

Sam can't take the torture anymore.

He keeps thinking this and it keeps coming anyway.

Dean has moved up to tickle over, around and behind his knees, up his thighs, above the line of his shorts, pausing to look pointedly between Sam's straining hard on and his face.

A spurt of precum escapes when he does this and Sam wildly hopes that Dean won't notice the wetness in the stupid heart patterned material.

Of course Dean remembers all Sam's ticklish spots from when they were kids and he pokes, wriggles and scrubs his fingertips in Sam's ribs making Sam howl.

And the panic is coming back now because the most ticklish place on Sam's body is under his arms.

Dean knows it and he's tormenting and taunting Sam, taking his time getting up there.

Sam struggles harder, trying so hard to pull his arms down against the ropes, pushing the rest of his body up as far as he can.

It's no use because there's very little room for movement and when Dean gets his fingers right into Sam's armpits Sam tries to scream but it just comes out as loud deep laughter, spilling right up from his belly, and he humps his body around as hard as he can to try and escape it.

There are tears in Sam's eyes and the two let him breathe.

Dean makes a few false starts towards Sam's armpits just to see Sam's body spasm and hear him beg.

The thrashing around has made Sam's hair all sweaty and Dean gently brushes the strands away from Sam's eyes.

Sam moves into the touch without meaning to and Dean's eyes flicker with interest.

John reaches out his index finger, stopping just short of touching the wet spot, leaving no doubt about what he's pointing to.

Sam's dick twitches up towards his hand.

"Tickling make you all horny baby boy? Tickling and kinky bondage and your big brother's and daddy's hands all over you?"

He feels all loose and sensitive from the tickling and he really really wants his father to touch his dick.

Sam at least wants to be able to keep still and quiet but he can't anymore.

He whimpers and rolls his hips, squirms and twists his head far to the side in shame.

The feeling of his boxer shorts being removed takes Sam completely by surprise.

He lifts his head to watch because this is different and John is crossing the line, just like that.

It's not only Sam's shame anymore if his father does this.

"Dad, what are you doing?"

His voice sounds deeper in his own ears, heavy with arousal.

John looks up, heavy lidded, eyes dark chewing on half of his bottom lip and Sam lets himself think, now, about wanting those lips wrapped around him.

"Want me to stop Sammy?" John keeps still, holding the elastic of the shorts but not touching otherwise. Sam allows his head to fall back his heart hammering at rabbit pace and dick throbbing so close to John's hands.

"No. Don't stop."

"S'what I thought." His shorts slide off and Sam anticipates a hand on his dick, prays for it, strains towards it, but Dean is back at the dressing table and Sam is completely exposed, ridiculous erection wagging around in the air.

Dean has a small red silky scarf, he ties it in a bow around the base of Sam's dick and Sam shivers at the feel of the soft material and groans at the humiliation.

Circling his little brother Dean smirked at his father and said, "Now if I remember correctly you have three main sweet spots."

Meanwhile lifting his hands up slightly to torment his brother.

John slowly raked his fingernails up and down his youngest son's inner thigh stimulating all the exposed nerves.

"Dean, please don't." Sam whimpered.

But Dean ignored his brother's protests as he lightly delicately teased his fingers up and down his brother's sides, and moved up to his lower ribs.

Sam lost it.

"Dean! N-no! Plehehehehehease!"

"Oh yeah, the lower ribs. Sweet spot number one." Giving an evil grin he continued to softly drag out that spot knowing slow torture turned him on.

"Deeheeheeheean! Don't! Stahahahahahahap!"

"What was that Sammy? Don't stop? Don't worry we weren't planning to at least for the rest of the day."

He slowly dragged his fingers up to his upper ribs before slowly reaching up into Sam's ticklish underarms, and stroking the hollows.

Sam gasped as Dean grinned.

"Not thehehehehere!" Sam begged.

He threw his head back slightly struggling less now as the tickling left him weak.

"Sweet spot number two!" Dean announced.

John meanwhile picked up a piece of string and slowly began teasing it between Sam's toes.

"Nohohohohoho! Deeheheheean! I-I c-can't t-take i-it! Hahahahahaha!"

Dean taunted, "Come on Sammy we're just getting warmed up here, you can take it, besides we've still got an entire few days of tickling and pleasure ahead planned for you."

"Now, where's sweet spot number three?"

He trailed his fingers back down Sam's ribs laughing at him as Sam shrieked and giggled insanely.

Dean was playing his ribs like a piano, with just enough pressure to make Sam go crazy.

He kept switching from his ribs to his underarms over and over again just to tease him.

Not remembering the spot without stopping his relentless torture he asked his father, "Where was spot number three?"

John replied, "I believe his spine and the back and sides of his neck."

Dean's fingers teased and stroked back up his chest, to his nipples, up to his neck as his fingers brushed softly at it.

They watched as Sam helplessly scrunched his shoulders up shaking his head from side to side.

Both men laughing at him and grinning at the torture presented on Sam's face.

Dean pointed to the table where there was a small paintbrush laying there, and his father reached over picking it up and handed it to him.

He watched as his eldest son dragged the bristles up and down Sam's sides torturously slow.

Then he began twirling it in Sam's bellybutton watching his reaction as he tried to hold in his laughter.

Their father grabs another brush and grabs Sam's left ankle in a headlock and slowly strokes his arch with the brush and feels his leg jerk as he tries to pull away.

"Sst-stop." Sam begged and pleaded.

John just shrugs and begins trailing over the tops of his feet as he squeaks.

He begins brushing over every ticklish nerve around his heels and toes.

"P-Please." Sam whimpered.

To both of them Sam was still begging and pleading, but they wanted to break him down to the least amount of syllables possible, so him talking now was unacceptable.

John moved to the ball of his foot and he jerks his leg again, a quiet gasp of ticklishness slipping.

Moving up to twirl the paintbrush beneath his toes, John smirked at his youngest, pulling them back and lightly dusting around each area making sure no skin is left untouched.

They hear him gasping and feel him tensing and just smile wickedly.

Swapping legs, John repeated the process on his right foot.

Dean meanwhile again begins to use his nails to spider over his ticklish underarms.

Seeing Sam's mouth twist he knows he won't be responsive any time soon, as his nails continue to spider relentlessly over his sensitive hollows.

His big brother began mocking his facial expressions as he dragged his wiggling fingers from his elbows, all the way down slowly to his hips, watching him try to twist and turn.

Smirking Dean continued to torture those soft underarms.

Then Dean changed tactics and moved to his neck, which caused Sam's head to jerk down.

He lightly brushed his fingertips over every inch of skin and behind his ears.

Sam's head jerks back in defense when he felt Dean's fingers on the back of his neck, as Dean lightly tickles just below the spot where he can't protect himself.

Dean's other hand brushes down Sam's ticklish throat and he jerks back forward.

Changing direction again, he worked his way up and down Sam's back finding a sensitive spot at the small of his back.

Sam squirms trying to fight the feeling of Dean's nails traveling slowly back up his spine to his neck, but feel them trailing down his chest.

He begins biting his lip as he watches Dean moving over his chest either a moan or giggle getting caught when he moves over his nipples.

Dean continues to tease him for a while there, and Sam tries to concentrate as he tries to keep quiet.

Picking up the brush again Dean twirled it over his right nipple, making Sam yelp.

He slowly trailed down to Sam's sides again tickling and digging into the curves to make him squirm.

He's clearly sensitive there but his hips are more attractive and they begin moving side to side he presses his fingers into them and rubs.

Sam's breath hitches as he tries to fight his body's need to move and assist the tickling torture, but he knows he can't resist.

Dean tells him this in his ear playfully licking the shell of it making Sam shiver, and squirm more.

Again he presses his fingers into his ribs and watches Sam squirm which only amplifies the tickling.

Then he takes the paintbrush and drags it across Sam's tummy back and forth agonizingly slowly.

His breath hitches again as Dean trails his waist but knowing it would be too easy there, he began trailing his abs instead.

He trailed down the middle of his abs to his navel and swirled inside the shallow part a bit.

Sam jerks back as the bristles toy with his nerves and Dean waits for him to crack, but this kid is stubborn.

John smiles and says "We knew your waist was ticklish so we figured we would move somewhere you're a little more sensitive."

Dean teases the paintbrush slowly across his waist and Sam jerks back.

Now he can only shake his hips side to side or thrust neither working to his advantage as they flutter below his happy trail.

Sam's lips quiver as Dean begins slowly painting from his chest to his hips and back down, repeating the short strokes up and down all the way across his waist.

John presses his lips below Sam's happy trail and blows, watching Sam yelp and jerk back.

Their father then reaches around his legs and runs his fingertips down the backs of his thighs, and hears Sam giggle.

He slid his fingers around the backs of his knees asking teasingly, "Ticklish here Sammy boy? Can't take it? You can take it a while more I think."

Snickering at his young boy's torture he moved between his legs and lightly scribbled his nails dangerously close to his crotch, knowing Sam could not orgasm for hours yet because of the cock cage.

Picking up the brush and drags the bristles over sensitive skin making Sam yelp and giggle, but then John begins moving to his weak spot.

John lets his fingers rest against the backs of Sam's knees, which are now coated in a thin sheen of sweat.

He squeezes the pressure points above his kneecaps to make his son yelp but he stops before he can laugh.

Dean taunts in his ear whispering, "Are you ready for this to end?"

Watching Sam nod eagerly Dean continues softly, "Then all you have to do is laugh" as he begins gliding his fingertips up and down his sides, and hips, across his tummy and down his thighs and settling on the backs of his knees, where they speed into a torturous dance over his sensitive skin.

Sam yelps as his head falls back and thunderous laughter shakes his exhausted body.

John moves a hand to his thigh and continues to softly tickle him there, moving his lips to blow a raspberry against his untouched knee.

A shriek shoots out of Sam as he laughs and pulls at the restraints. They begin blowing and blowing again until they finally stopped and Sam becomes silent.

Taking a slight break they allowed Sam a little water before Dean continued on with the next part, which would be more sexual than just tickle torture, maybe play with the cock cage a bit to tease Sam.

Coming back over to Sam, Dean has a riding crop in his hand, as John is on the sidelines watching.

The big brother grins at his brother's helpless exhausted body and lets the crop trail down his brother's body until he can gently tap against the cock cage.

Squatting down Dean cups Sam's balls rolling them playfully in his hand, making Sam hiss.

Dean remarks, "You're really full while we're at it I might as well milk you now considering we've been going for a while, and we are going to make you orgasm repeatedly non stop all day for another few days and there's nothing you can do about it."

Sam's whole body tenses on the bed when he feels Dean lean behind him slightly, and feels a cold, wet finger press against his hole, teasing the muscle.

He feels the whole finger inside of him, gently moving around.

Dean makes an approving sound and Sam is sure his face must be a beet red by now, but there's nothing he can do about it.

A second finger soon joins the first and feels Dean scissoring inside of him.

It lasts only several seconds until Dean hits his sweet spot inside of him that makes Sam see stars and lets an involuntary moan escape him.

"Like that huh? Just take it for me Sammy." Dean teased softly and starts rubbing his prostate relentlessly quickly reducing Sam to a whimpering shaking mess.

Dean grinned at the thought of power he had over Sam's naked body right now because his little brother was tied to the bed helpless, so all he could do was lie there and take it.

Sam looks down between his legs in time to see the first drop of milky white cum falling from his still bound cock.

He turns away and tries to ignore the waves of pleasure running through him.

Dean does not stop until his balls are nearly empty and Sam barely manages to stay put.

He hisses when Dean adds a third finger and teases, "You are doing so well Sammy, almost can't believe you're a virgin, you open up so nicely for me. I bet that annoying pressure in your balls is gone now."

His big brother continues to relentlessly tease and fuck him with his fingers, though Dean avoids touching his prostate, which drives him crazy.

Grabbing a brush while relentlessly teasing his little brother with his fingers in his ass, he reaches forward with the other hand and tickles Sam's balls knowing they are so full that it hurts Sam.

He just keeps stroking though ignoring Sam's pain or pleasure and reaches down with his hand to cup them in his palm and roll them again.

Dean remembered a night when Sam had the cock cage on and vibrating plug in his ass as they were all sitting watching TV with their dad on the couch with Sam in the center leaning back against Dean's chest.

And Dean and John would spend hours just softly tickle torturing him in different positions knowing he couldn't get away.

Then one would wrap one hand around the cock cage holding it still while ordering him to spread his legs wider, and one of them would pull and push the plug in and out of Sam.

They would test the remote control on different levels bringing Sam to the edge many times, but not enough to let him orgasm.

They would then playfully push two fingers in and Sam would let his head fall back resting on Dean's shoulder.

One of them would play with him for close to an hour just gently fucking him with their fingers relentlessly.

Dean thought maybe today they could do that to him again, he felt like Sam could take it, so he would bring up the idea to his father once they were done here.

Feeling Sam desperately trying to fuck himself back on his fingers he continues to tease his prostate slowly and his moans are like music to Dean's ears.

Keeping an eye on the strips of cum from Sam's soft cock he tries to coax even the last drops out of them.

Stopping for a moment, Dean leans in and says, "We will limit you to orgasms as we say today and tonight and I can't promise I won't tease and edge you for a few hours before each one."

Sam lets out a sob as Dean slowly pulls the cock cage off his cock and torments, "Don't worry, Sammy, I'll make you feel so good. Look at that, barely out and you're already almost completely hard. Someone seems to be really desperate, huh?"

Dean kneels between his brother's legs watching him squirm, and Dean isn't sure if he tries to get closer to him or away, and he smirks.

There are tears on Sam's cheeks and Dean gently traces the length of his cock with his fingertips.

"You really want to cum, don't you? Say it." Dean teases.

Sam looks at him with pleading eyes and he sounds like he's begging.

"I want to cum. Please, Dean. _Need._"

Dean continues to play with him just like this stroking his cock slowly up and down, and normally Dean preferred to play with his baby brother for quite a while more, to make him break down to monosyllables but not now.

So he just wraps his hands around Sam's dick, using the precum collected at the tip to properly jack him off.

As expected, it doesn't last long.

Sam is a moaning mess in seconds, and when Dean reaches up to give one of his nipples a gentle tug he's gone.

Dean removes the cock cage as Sam begins shooting his load all over Dean's hand and his own chest.

Dean laughs at him through his orgasm, enjoying the sight of a heavily breathing but completely blissed out Sammy.

When he's done, Dean cleans him off.


	2. Chapter 2

Day One Part Two

Urging their father to join in with him, they once again begin Sam's tickle torture session after the sexual pleasure.

He watched as John lightly ran the fingertips of each hand very slowly up and down Sammy's trapped and sensitive soles.

Their father could feel the muscles under the smooth taut arches twitch uselessly as they tried desperately to escape his tormenting fingertips.

John began moving his wiggling fingers even faster along his soles, raking mercilessly along the tender arches moving up to the unbearably sensitive area under his toes.

Dean then brought two tiny paintbrushes to Sam's underarms again trailing the tips through the hair of them, teasing both armpits relentlessly.

His big brother teased him, "Man Sammy your cock is so fucking hard right now. You like this don't you baby boy?"

Reaching out John gripped his son's stiff penis and stroked firmly slowly, up and down its trembling length.

Sam groaned as his body became rigid with tension as he was edged closer and closer to the very verge of his much needed orgasm.

His father pumped his cock 10 to 12 times relentlessly until it was obvious that one more stroke would bring young Sammy off.

Then he let it go, watching it bob in the air with need, glazed with a thick coating of pre-cum.

Sam groaned loudly in frustration, his sweat soaked abs strained mightily to buck his hips and fuck the air, but his bondage hampered his ability to do so.

Giving Sam a moment to catch his breath, they decided to slow it down and return to the agonizingly slow tickle torture.

Dean leaned forward saying wickedly, "Hey dad watch this, I can keep Sam from orgasm for hours just like this, but bring him to the edge as many times as we want."

He carefully ran a fingertip lightly and slowly from the boy's knee to his groin.

As he moved it gradually upwards, he wiggled it backwards and forwards.

With nothing protecting Sam's sensitive body Dean knew he could feel the lightest touch.

Sam begged, "P-P-Pleasssee t-that t-tickles."

He ignored his little brother and repeated the process on the other thigh and then using both hands he began stroking his fingertips very lightly all over the boy's legs.

He paid special attention to the backs of his calves and his knees, and concentrated particularly on the insides of his thighs.

Sam began squirming under the restraints moaning softly as the fingertips lightly ran over his legs.

His cock was now stiff with attention at the light touches.

For ten minutes Dean did nothing but glide his fingers over his skin lightly stroking, teasing, and caressing.

Sam began following the movement of his big brother's fingers as they glided lightly over his legs and thighs.

Dean smiled to himself knowing just how horny the boy would be in a few hours.

He waited until Sam's knees were fairly close together, and then pushed a fingertip deep into one of the creases sliding it up and down.

Sam gasped making Dean grin as his cock grew to full erection.

Dean removed his finger and continued teasing his little brother as he had been doing for the last ten minutes.

A little later he repeated the same gesture but this time he pushed his thumb into the crease at one side and two fingers into the other side.

He gripped the root of Sam's cock and massaged it slowly for a few seconds.

Smiling as he heard Sam moan with his eyes closed, he pulled his hand out and continued tickling the boy's legs relentlessly.

Again he began to trace his fingertips up the inside of his thighs but this time he didn't stop when he reached the top.

Instead his fingers continued onto the boy's balls tickling lightly.

Hardly touching he ran them around and around the sensitive area.

This time he tickled the sides of his balls and when the boy's movements raised his body off the bed, Dean took the opportunity to tickle the back of his balls and the crease between the cheeks of his ass too.

He knew this was not just for the fun of making Sam giggle and laugh helplessly at the slightest touches, but it made the boy more and more aroused, as he began to sweat.

Dean tickled the boy's balls efficiently and mercilessly.

After another minute or two of this torture he thought time to return to the boy's cock.

He weighed on the possibilities for torturing the boy's cock and thought the vibrator would be perfect.

Dean knew he would have to be very careful, as he knew vibrators made people orgasm very quickly, and the one thing he did not want was for his little brother to cum.

Not for a long time anyway.

He plugged the device in and switched it on.

Carefully he touched it to the tip of his brother's cock-head.

Sam closed his eyes tight, throwing his head back, and moaned.

"Aaaaaahhhh."

Dean began removing it.

"No! Please! Put it back!" Sam moaned.

Dean smiled wickedly and replied, "Okay."

Again he touched it lightly to the sensitive cock head just for a couple of seconds.

Hearing Sam moan again in ecstasy was like music to his ears, knowing all he could do was lay there and take it.

Removing it again he heard Sam whine, "Please-Please put it back and leave it there."

"Oh no." Dean replied knowing that more than a few seconds of contact with his cock-head would make Sam orgasm.

He put the vibrator down and picked up a gag.

Forcing it between his teeth he strapped it tightly around the back of his head.

There was one thing that was important which was Sam be rendered incapable of talking all together.

Satisfied that the boy was unable to say anything understandable, Dean took a small feather from the table by his side.

He began to stroke the pointed tip lightly over his naked and sensitive balls.

Sam groaned, then started to giggle, then to laugh, then began to struggle wildly in attempts to get away from the unbearable horny tickling.

His thigh muscles tensed as he tried to close his legs together, to protect himself, but he knew since his ankles were bound to the bead spread eagle so he couldn't do anything to escape it.

Dean followed his movements continuing to tickle the boy's balls sadistically.

The curve of the feather enabled the tip to reach underneath and into the deepest and most sensitive recesses, driving the boy into hysteria.

For a long time Dean continued this relentless torture moving the boy's dick down until the cockhead was accessible.

They had been at this game for a couple of hours now, and the middle of Sam's thighs toward his crotch was swimming with precum.

He gently encircled the base of the boy's cock with his fingers of his left hand and pulled it downward a little.

Dean had found that this usually increased the sensitivity of an already horny cock very much.

Sam groaned, confirming the theory.

With infinite precision, Dean placed the palm of his right hand half an inch above the tip of the boy's cock-head, and closed his thumb and fingers together until they just touched the shaft of his dick.

He moved his hand upward, tracing along the shaft of his cock and then over the ridges and head until his fingers came together over the tip and slipped gently off the end.

Sam made a sound halfway between a groan and a scream his eyes wide open staring at his fingers.

"Mmmmmmnnfffkkkk."

Dean repeated the movement, slowly only this time he also allowed the palm of his hand to touch the edge of the foreskin, where it gathered around the piss-slit.

An electric shock of intense pleasure jolted through the boy's nervous system and he moaned again in ecstasy.

Sam's hips thrust upwards trying to push his needy cock further and harder into the far too loose grip of his brother's hand but Dean was having none of it.

The effectiveness of this fiendish torture depended on the victim's being totally unable to control the amount of friction he got on his cock, and never getting quite enough.

Dean followed his movements easily with his hand, not allowing him the slightest bit of additional stimulation.

When Sam began thrusting hard and fast, he simply took his hand away altogether.

Sam moaned and groaned around the gag, saliva running down the side of his chin.

He released the base of the boy's cock while continuing the light grip and slide manoeuver, and began gently tickling his balls, inner thighs, and perineum all at the same time.

Sam began squirming again and fighting against the restraints in earnest.

Dean knew exactly how much his little baby boy needed to orgasm, and he found the more his brother turned him on, the more sadistic he became working on his helpless baby brother.

He picked up the small feather again, holding Sam's cock firmly around the base once more, stroking the soft tip over the engorged, precum oozing cock-head, focusing on the ridges of the head, the edges of the foreskin, and the piss-slit.

Every so often, he changed from that to rubbing the tip of his thumb in small circles over the frenum the sensitive spot below where the ridges come together on the underside of the cock-head.

He knew from experience on most other victims that that spot more than any other made them need to orgasm most urgently.

Each time, after just a few seconds, he went back to using the feather, and each time Sam thrust his hips and groaned in frustration.

Dean worked on Sam like this for another fifteen minutes, by which time his little brother was beside himself with the urgent need to orgasm.

Reaching down to the table, he slipped a black condom like sheath over Sam's cock.

It had a lump on the end of it, with wires leading from it, which he plugged into a small battery – operated box.

After setting the controls and placing the box on the floor he smiled at Sam wickedly and said, "Let's have some different kind of fun now."

He and his father smirked as he switched the device on and a tiny vibrator began to buzz at the tip of the sheath.

It stayed on for three seconds, switched off for ten, and then repeated the movement.

As it began to vibrate they stood back and watched pleasantly as the boy arched his back and moaned loudly in ecstasy, but as it stopped he yelled and swore in desperate frustration.

After about fifteen twenty minutes of them just watching with amusement at Sam's frustration, Sam was moaning and writhing in his restraints on the bed.

At first it looked like he had cum, as there was a large pool of spunk between his thighs, but was only precum, which had run down the inside of the rubber.

Dean could see Sam trying to say something and he knew exactly what he wanted.

Sam wanted him to leave the vibrator switched on so he could orgasm.

Just then the vibrator began to buzz again and the boy's gag-muffled words deteriorated into grunts and whimpers.

Dean reached down with a smirk and adjusted the controls on the box reducing the on button time of the sheath to just one and a half seconds.

Then he began to again stroke and tease the boy's balls and inner thighs at the same time as it worked on his cock.

This increased the intensity of the torture to unbearable levels.

Sam writhed and struggled on the bed while Dean's fingertips danced, teased, and tickled his balls and the vibrator buzzed on the tip of his cock.

The vibrator stopped and Sam shook his head from side to side in desperation.

"Noooo." Sam moaned.

Smiling Dean turned the vibrator off and removed the sheath.

A further stream of cum ran out of the black leather as he took it off.

Sam's cock was coated in a thick film of his own lube.

He looked for a moment at the beautiful boyish face gazing imploringly up at him.

"I would love to look at your face for a long time Sammy, but I'm afraid it's time for you to feel a lot more helpless."

He reached out and took an object from the table it was a thick black blindfold.

Leaning down he strapped it over Sam's eyes and tied it firmly to keep it there, and making sure it was completely light proof.

Sam blindfolded, and tied up he felt more helpless and vulnerable than he had ever felt in his life.

Taking the insanely desperate cock in his hands, Dean went to work on it with all of his skill.

Noticing his father had once again joined in as he tickled Sam's feet excruciatingly slowly as Dean caressed his cock gently, stroking the shaft lightly teasing the head palming the tip, sucking the cock-head and tongued the tip through the mouth-hole of the balaclava.

He tickled Sam's balls relentlessly slowly and his inner thighs again and pushing the tip of a finger gently into his hole.

Dean was a master at manipulating Sam's need for orgasm.

The big brother knew many ways to intensify his need to orgasm until it became so compelling that it took over his entire consciousness and was the only thing he was capable of thinking about.

And now he used every single one of those techniques on him again.

This was totally unbearable he could see for his sweaty pleading baby boy.

The boy struggled, writhed, moaned and thrust his hips pushing his cock further into his teasingly light grip in maddened convulsive attempts to get himself off.

Under the blindfold Sam was desperately pleading and begging Dean to make him orgasm, but the gag reduced his words to unintelligible croaks.

It seemed to him that Dean was paying no attention at all to any of this as he continued to tickle the boy's cock, balls, and thighs infuriatingly lightly and slowly, sadistically denying him the friction he needed.

But in fact Dean was paying very close attention and taking advantage of his helpless little brother.

Dean was in a sadistic heaven working on that sexy horny brother like a thing possessed, and continually tried to find ways to make the helpless kid's torture even more unbearable than before.

Because Dean's soft touch was so infuriatingly light it was getting progressively more sensitive by the minute.

After about another hour, Dean decided it was time for phase three.

He took Sam's cock gently in one hand and began to wank the boy very slowly using his thumb on the underside of his cock and his fingers on the top.

Dean's fingers slid slowly up and down his cock, lightly stroking the sensitive ridges of the cock-head now getting Sam closer to orgasm every moment.

But then Dean stopped.

His hand remained around Sam's cock, holding it but it was now stationary.

Watching Sam scream into the gag made Dean and his father grin as he tried to get that little bit more friction that would send him over the edge but Dean carefully denied it to him keeping his hand still by following Sam's movements.

When the helpless kid gave up and collapsed back onto the bed, Dean started wanking him again just as slowly and lightly as before.

He was only using one hand but eventually adding the other.

Within seconds Sam began to struggle and moan again and Dean took him as close as he dared to orgasm before stopping once again.

Dean nodded to himself as he realized through Sam's moaning that when he felt the orgasm approach the moans got more intense, more urgent.

He would use this to his advantage over Sam.

Again he waited until the boy had stopped struggling and then commenced working on his cock.

Slowly up and down, up and down the boy was yelling and swearing and threatening around the gag and Dean stopped.

After a few more times of bringing him close to orgasm and then stopping, he was pretty sure he had the measure of Sam's reactions.

He could get Sam closer to the edge every time.

Dean took his brother to the edge of orgasm again and stopped again, just a second before Sam was able to orgasm.

The only thing they could recognize coming out of Sam's mouth was "Mmmfffmgghhhcccmmmccmmmfffkkk."

Dean just smiled at his baby boy's helplessness in the situation, as he knew precisely how much Sam was suffering.

He started wanking Sam's cock again using the same technique as before, but now also tickled his balls and inner thighs again with his other hand for good measure.

Occasionally he slipped his fingertip gently into the boy's asshole just to make it worse and to make Sam want to desperately orgasm even more.

It took even less time to get him to the brink of orgasm now, but Dean could pick up the signs and could stop just a point away from no return.

Again and again Dean took him to the edge, only to stop just too soon.

Sam could do nothing but struggle and lie there and take it.

Then the fingertips began their fiendish torture again.

Dean suddenly thrust his other hand between his thighs from the back, the thumb and fingers deep in the crevices at the sides of his balls, where he knew it was the most difficult to resist, and began to both massage the root of his cock and to tickle his balls.

Sam could feel the orgasm approaching again slowly and inexorably, as Dean's hands so lightly teased, tickled, massaged and wanked.

He knew though that Dean would not let him orgasm yet.

Sam flung himself around as far as the restraints would allow of the torture of the relentless teasing fingers.

But wherever he moved the hands were there, following him, teasing, tickling, slowly wanking getting him closer and closer to orgasm.

Dean didn't stop completely but he slowed down so much that Sam just couldn't quite make it.

He was suspended on the very edge of orgasm.

Eventually Dean's fingers froze as Dean kept him there, and Sam felt himself back off again from the point of orgasm yet again.

But then they started moving and it was there again at the edge.

Again Dean's fingers slowed for an agonizing few seconds, then stopped.

He repeated this four or five times taking the kid to the edge and then backing him off slowly never allowing him more than a couple of heartbeats before he started again.

Reaching forward with one hand while continuing to caress the boy's cock gently with the other Dean removed first the blindfold, and then the gag.

As soon as the gag came out they heard the words, "Please… Please… Let me cum. I'll do anything you want but make me cum!"

A slow smile spread across Dean's face. He'd got him.

He held the boy's cock gently in his hand carefully keeping his voice neutral he asked, "You want me to make you cum?"

His fingers began to slide slowly up and down the rock hard cock again.

"YYYeeess."

Dean paused, considering this "Let me make sure I understand. You want me to make you cum?"

"Yes! Yes! Please! For God's Sake make me cum!"

Sam was on the very edge of orgasm again and his fingers stopped moving for a moment.

"You want me to wank you off?"

Sam's voice came out in an urgent, "Yes! Yes! Yes!"

As a little incentive Dean moved his thumb gently up and down just once over his cock-head.

"Yes!"

"Okay you've got yourself a deal."

Dean leaned over the boy, and slowly lowered his head until their lips were inches apart.

At the same time he gripped Sam's cock with just a single finger and thumb and began to slide the foreskin backwards and forwards over the head as slowly as he was capable of doing.

Sam stared wildly into his big brother's eyes.

Dean could feel his brother approaching orgasm again as his cock stiffened even more and he started to moan.

All this time the brothers' eyes never left each other's.

In slow motion keeping his eyes on Sam he used his fingers to slide the foreskin over the hypersensitive cock-head bringing Sam screamingly slowly towards orgasm.

His sadistic older brother made the approach as prolonged as humanly possible his fingers now almost not moving at all.

Sam was staring wide eyed and not breathing as Dean lifted his head towards Sam's and their lips met, tongues intertwining in a passionate kiss through the balaclava.

A second later Sam began to orgasm convulsing and shaking in his restraints as his spunk shot out of his cock.

Pulse after pulse of hot spunk shot upwards into the air unseen by either of them.

Dean's fingers now slipping on the spunk coating them, didn't speed up his strokes one bit, but maintained the torturously slow milking of Sam's cock.

The spunk continued to spurt ten, eleven, twelve, thirteen fourteen then fifteen times and landed everywhere.

His cock continued to jerk and throb under Dean's fingers, but now nothing more came out.

He was still shaking and still cumming as he kissed Dean while he continued to dry milk him as Dean laughed at him.

Dean let him settle cleaning his brother off and they decided to give him a minute break before their dad could have his turn to torture Sam for a while.


	3. Chapter 3

Day One Part Three

After a minute rest was up, John moved in leaning against the whimpering boy as he again placed the blindfold over his eyes and tied it.

Once again he also tied a rag in Sam's mouth to gag the boy.

Experimentally Dean watched with a grin as his father ran his fingertip lightly up the inside of their boy's thigh.

Sam tried to snap his knees together as he began struggle and to giggle uncontrollably.

John smiled wickedly down at his son and instead of pulling his hand out he pushed it slowly upwards towards his youngest son's balls wiggling his fingers even more.

The helpless boy was hysterical.

Sam was shaking his head violently moaning and struggling like mad to get away from the tickling hand.

He moved closer and continued pushing.

John made contact with the bottom of Sam's balls and cupped them in his fingers tickling them lightly and slowly.

At this, the boy's moaning became even louder and his struggles more violent.

A dark patch of precum began to spread from the tip of Sam's hard cock.

Memories of tickling Sam and Dean as kids came back and he brought his other hand up probing deeply just below the boy's bottom rib at his side.

Sam screamed into the gag trying hopelessly to close his arms to his sides as tightly as he could to protect his ticklish sides but the restraints made it not quite possible.

John's hands were all of a sudden all over the boy tickling and teasing deep into his underarms digging into his sides, squeezing just above the knee, or the back of his helpless squirming thighs, tickling his balls agonizingly slowly and teasing his cock.

Sam yelled, bucked, and writhed on the mattress at every touch, his knees squirming spasmodically but he was unable to stop the relentless tickling.

John continued to tickle torture his helpless younger son sadistically slowly, then gently took the hard cock and began to wank him off slowly.

Sam fought like crazy to get away from his hand yelling into the gag but couldn't get away and very soon the gentle but relentless milking was made even more irresistible by his father's other hand tickling his balls softly.

As much as he tried to stop himself from cumming again his spunk shot out helplessly into his father's slowly moving fingers in huge sticky gobs.

Once his orgasm was again over the exhausted boy lay there panting as the older brother and father smirked down at him as John began to wipe the boy down.

Dean suddenly recalled another thing with tickling that brought Sam to arousal and that was blowing into his tummy.

He leaned forward gently patting Sam's stomach lightly just teasing it as he removed Sam's gag wanting to hear him before blowing into it with all he had.

Pressing his face into Sammy's tummy he blew his breath out making the farting noise.

His lips flapped against the skin causing Sam to giggle loudly.

He made repeated blowing sounds against his more sensitive lower abs, and groin, causing him to jerk upright, squealing in ticklish agony.

The intent however was to keep his erotic and ticklish sensitivities inter-mixed.

More and more his ticklish areas elicited increased erotic reaction when it was orally stimulated.

With the mix of blowing, Dean's tongue deliciously swirled along his lower torso.

"Gahhaahh! Uuuhhh! Ahhhhaaagghhaa!" Sam cried out.

For over half an hour, Dean kept this particular teasing going.

He could see his precious little brother was becoming more sensitive.

"Wwwwwaahhhh Grrruuuaaahhhhaahahahaha."

When Dean felt a further, stiffening in Sam's erection he turned his attention to his nipples.

At the first touch of the tongue, Sam went crazy.

"Yyyuuuuhhhnnngggrrruuuuhhhgggrrrraaaggggooodddnnneeess."

Just the reaction Dean had been expecting and wanted.

Those luscious nipples and pecs now were hyper sensitive.

Dean kept a constant swirl from the nipples, to the side of the pec, tracing along to the underside of the pec, back to the nipple.

Merrily wriggling fingers lightly danced along the side of the opposite pec, then back to the other nipple.

Sam's body was steady quaking and shaking.

"GRUUUHHNNUUHHWHHUUNNUUHHNUUHHNNNGRUUHHUUHHNNGG!"

Ten minutes went by, and tears were streaming from Sam's eyes.

Twenty minutes saw him sobbing.

Now, Dean's fingers wriggled along the sides of both pecs, while keeping up the lavish nipple tonguing.

"WHUUHHUUHHUUHHUUHHUUHHUUHHUHHUUHHUHHUHUUHUHUH!"

Forty-five minutes of intense nipple teasing, had Sam in a state of loud,  
growling babble.

Dean was pleased to feel Sam's aching erection pulsating forcefully under him.

He slid off the bed to retrieve one of two, dried out felt-tip pens that had been soaking in water.

Dean stretched out on the bed, his head at Sam's right foot.

Pulling back slightly on Sam's toes, Dean pressed the tip of the pen in the middle of  
the sole, and made short up/down strokes.

"WWHAHHAAAIIIIEEEEEHEEEE! YYAAAHAAHHAAHHHAHHHAAHHAGGH!"

Sam's feet were at a hyper - sensitive ticklish level that sent him  
straight into hysterical warp-drive.

This was the first time he reacted like this, when tickled on this area of the right foot.

Dean felt that now familiar rush building up.

The short strokes with the felt tip in the middle of Sam's foot became shorter strokes.

"GAHGGAAHHAARRGGAAHHAHHAARRRAAHHAAARRAAHAHH!"

Sam was twisting, bouncing, bucking, and screaming like a wild man.

Dean thought about the more sensitive ball of Sam's bare foot, and the rush he  
felt increased its build-up.

He fought the urge, and kept tickling the middle of Sam's bare sole.

The rush was close to overtaking him, so Dean stopped.

It took a couple of minutes for Dean to settle down, and for Sam to stop  
twitching.

Dean noticed that Sam's toes were still flexing.

He pulled the toes back again, and the felt tip visited each one, the baby toe first.

Rapid up/down stokes at the base of each toe had Sam howling.

When he reached the big toe, he swirled the felt tip in a circular motion at its base.

"GAAHHGAAHHAAHHAAHHAAHHAAHHAAHHAAHHAAHHAAHHAAHH!"

Dean switched to an up/down motion for a minute or two then slowly dragged  
the felt tip downward, across the ball of the foot.

He circled the pen around the ball then made curly-q's around and across.

Sam returned straight away to ticklish-warp-factor-nine.

"HHHHHEEEEEEEEEEEEEEEEEEEEEEEEEEEE! HAAHHAAHAHHAAH!"

After ten minutes of this, Dean couldn't take much more: holding off the  
surging rush was too great a task.

He whirled around, climbing atop the bed, and slid straight for Sam's bouncing hard-on.

Taking it in his mouth full length, he expertly bobbed his head in a steady fashion.

His tongue slid along the underside of Sam's shaft, while he applied just a small  
amount of suction.

Dean had sent Sam into sensation shock.

Sam's legs still trembled, and his toes still flexed in ticklish reaction.

Reactively, his hips drove deep into the mattress when Dean's lips pulled back to the swelling head of his erection, then up when he slid down.

"GGRRUUUHHAAHH! AAHHAAHAAHHAAHHAAAARRUUUUHHH!"

Dean began teasing the head, lingering there with rapid oral strokes, then  
sliding back down the length of the shaft.

In just a few minutes, Dean heard Sam change pitch to a still loud, yet bubbling growl.

"HHHUUUNNNGGRRRRR! GRRUUHHUUUUUNNGGGRRUUGGRR!"

He picked up the pace.

With his hand, he stretched the skin back taut, his lips gliding back and forth, going no further than just below the head. 

Sam's pulsing, pumping shaft swelled even more.

He stiffened, shuddered then erupted violently.

"HHHUUUUNNNNGGGGRROOWWWAARGH!WWAARRGGRRUUHHNNGGRRAAGHH!"

Steady, without letting up, Dean continued orally stroking Sam's  
erection, which felt as if it stretched some more.

Sam was screaming and growling like crazy.

"GROWAARRGH! HOOSHHEEEEIIITT! WWAARRGGHH!"

Dean kept at it for a few minutes more. Just to satisfy himself he slid  
up to Sam's chest, hungrily lapping his nipples.

"WHHUUUUUUUUUUHHH! GUHHGGUUUU HHDDGGRR AA AAASSHHUU USSHH!"

A couple minutes was just about enough. Time for that much more ticklish left foot.

Trembling, Dean grabbed the other soaking felt tip, twirling in a slow path from just below the middle of the sole to the base of the toes. 

"YAHYYAAAAAAAAAHHHHAAAAAAAHHHGGG!"

"HHAAAAAAGGGGAAAHHAAHHHHAAAGGAAAHHH!"

"YOOOUUHHAAAHHGGAAAHHAAAYYOOUUUUUUUUDRIVINMEEEEKKAAAHHAAAAHHKKRAAAZEEEEE!"

Dean strained a look back.

Sam's hips were slamming the mattress. 

Definition in his arms and chest muscles were pronounced, so taut were they  
against the restraints.

Mouth agape, screaming.

His head was snapping side to side with his body arching, twisting, shaking, and glistening in sweat.

Sam's erection with its wonderful curve standing at full attention, what a beautiful picture!

The rush surged forth, unabated.

Dean's eyes grew heavy, the felt tip falling from his hand.

Instinctively, his fingers danced a wrigglish, grazing tickle dance on this hyper sensitive barefoot.

His body trembling, Dean swayed drunkenly.

More surprising, he hung on for a few minutes, tickling Sam's foot to the sounds of increasing hysteria.

Finally, Dean slid off the end of the bed, curling in an orgasmic scream himself.

The floor, the room, everything seemed to be floating.

There was no sound. 

Dean purely was in a euphoric state.

He rolled over. Looking up, he could see Sam's feet flexing forcefully.

His legs appeared to be jumping against the ropes.

Dean grappled with the sides of the bed, willing himself up against the bed.

The sight that met his eyes as they rose high enough, took him by total surprise.

The haze surrounding Dean finally cleared, and his ears opened up.

Sam's body wasn't twitching he was jerking, and still laughing!

Dean crawled to the dresser. Reaching up, he found the new extra long,  
athletic shoelaces he bought a couple days earlier.

The older brother busied himself, attaching one end to the rope around Sam's left ankle.

He then looped the lace around each toe, then back thru the rope.

Dean gently tugged the loops, stretching back each toe.

When he tied the other end off, he licked Sam's' foot at the base of the toes.

Sam's foot jerked, but the toes could not flex.

Satisfied with his handiwork, Dean did the same with the right foot.

He went to the bathroom to relieve himself, and wash off.


	4. Chapter 4

Day One Part Four

Not replacing his shorts, he also stripped off his T-shirt, and socks.

Returning to the bedroom nude, Dean replaced the felt tip pens in the small water filled cup on the dresser.

There was another cup with several Q-tips soaking in it.

He took two of them, sat on the floor, with Sam's feet in front of him.

Q-tip in each hand, he slid them between the big and second toe of each  
foot.

Sam immediately bucked.

When Dean began rotating the Q-tips between his thumb and forefinger, Sam howled.

Ever so lightly, the Q-tips tickle-teased each gap between the toes.

Each of those ticklish gaps were revisited several times.

"GEEGEEGEEGEEGEEHEEHH! HAAHAAHAHAHHHAHHA!"

When Dean felt sufficient time had passed, the Q-tips swirled to base of the  
big toes.

The decibel level rose.

Dean wiggled the Q-tips across the width of each foot along the base of the toes.

He wanted Sam right where he was when the first rush hit him.

Not satisfied, Dean dropped the Q-tips, and grabbed both felt-tip pens.

They attacked the ball area of both feet.

"WHHHAAAAAAAAAAAAAAHHHHHGGGGGGG!"

"YA AHHHA AHH! HHA AHHSSHHHEEIITT!"

"SHHEHHHEEEEHEHEEEEEIIIITTT!"

Feeling the itch slowly tingling between his legs, Dean smiled.

The felt-tips were drawing circles, figure eight's, straight lines, the works. 

Sam was in a screaming hysterical fit. His hard-on had not lost its  
stance at attention.

For fifteen minutes, Dean tickled the ball areas of  
both feet, until his brother started slipping into silent hysteria.

Then he slid the felt-tips down to the middle of each sole. The screaming hysteria  
returned.

"NOOOOOOOO! NNOONNOONONONOOOOOOO!"

"DONTWHAAHHAAAHAAWHAAHHAAHHAAHDONT!"

"HAAAGGHHAAHHDRIVEMEEEHHEEEHHAAAHAA!"

"HAAHHHAHHAHHAHHNUUTSSSWHEEEHEEEEEE!

Over and over again, Sam was screaming not to drive him nuts.

This was the first time Sam had ever hysterically pleaded.

Dean felt his own erection growing again in satisfaction.

Sam's babble hysteria was sweet! 

Dean noticed Sam's nipples were so hard they took on a smooth, rounded  
appearance.

Sam was bucking in the bed so violently, the legs were chattering against the mattress.

His mouth was babbling in silence once more, so Dean dropped the pen in his right hand, choosing to orally tickle the left foot with his teeth.

The sweet sounds of Sam screaming again.

Deliciously ticklish like never before, the taste of Sam's feet sweeter than ever, he continued tickling them with increased vigor.

"WHAAHHAAHAAAKAAHHKKAAARRAAHAHA!"

"KAARRAAHAAHAAKAARRRRLLLYOOOUUUHAAH!"

"AAHHAHHAAARROTHHAHHROTTENASSAHHAAHH!"

Sam's erection was dripping once more.

Dean kept working his teeth against the ball of Sam's left foot, but dropped the felt-tip and let his fingers dig into a wriggling tickle job on the right foot.

This seemed to shift Sam's screaming hysteria into screaming growls.

"GRRRAAHHAHH! GGRROWWWAARRAHHAAH!"

"GRRAAWWAAHHAAHHAAGRRAAHHAAGGRRAGH!"

This caught Dean's attention.

His erection started throbbing.

He saw Sam's hard-on steady pulsing out clear ooze.

Excitedly, Dean scrambled to Sam's bedside, swallowing Sam's membrane.

As he slid his oral cavity up and down Sam's shaft, it stiffened harder than the previous time, pumping cum in a steady, even flow.

"GRROWAAARRWHAARWHAARWHAARWHARR!"

Sam was thrusting his hips upward hard and fast.

Dean held his head steady, allowing Sam's rock-hard love shaft to thrust between his lips. 

He realized that this was only the first lava flow.

Truly growling this time like a bear Sam thrusted into Dean's mouth for another two minutes. 

Dean felt an incredible increased stiffening in Sam's cock, and began  
stroking his own.

The tidal wave was rushing upon him now.

Sam went silent for roughly thirty seconds.

Encouraging him gently Dean taunted in his ear, "Don't hold back baby come on cum for me."

Then, his hips were thrusting in long, violent jabs. Immense animalistic roars of deafening proportions, simultaneously released with four gigantic spurts.

"GGGRRRAAAAAARRGGGRAAAAARRGG! HHHAAARROOWWWAAAHHGGROOWWAAR!  
MYYYGGGOOOODDNEEESSS! HHAARRRGHH!"

Thrilled... no, Dean was overjoyed and surprised at both the heat, and  
amount of flow that erupted from Sam. The tidal wave rushed over him.

Giving him a few minutes to settle down and breathe, Sam jumped a little at the sudden soft caress of Dean's finger at his entrance, softly teasing.

As Dean did so, a hand massaged gently at his balls and he knew his father's touch, the calloused fingers rolling his balls just as he liked.

Sam let out a huff of breath, relaxing into the touches of both his brother and his father, a soft 'oh' escaping his lips as Dean's finger slid in knuckle deep.

"That's it Sammy, just let us play with you." Dean assured him, his free hand a firm presence in the middle of his shoulder blades.

Sam squirmed as Dean began to finger fuck his hole, his father's fingers massaging his balls and cock.

He was getting hard again as he shifted his hips as much as he was allowed.

"Such a greedy boy." John teased behind him, his free hand caressing and massaging into his ass cheek.

"Mmmmm," Sam hummed in response before groaning, hips shifting further as Dean crooked his finger and dragged it delicately along his insides.

He pulled out before he pressed for entry with two fingers this time, watching as Sam pushed back to accept them.

"Oh Dean."

"You enjoying yourself baby?" Dean asked him with a chuckle.

"Yessss." Sam replied, hanging his head, and letting out a gasp, John's fingers wrapping into an 'o' around his shaft and gliding up and down in rhythm to Dean's fingers spearing in and out of him.

"Oh fuck yes yes."

Both his father and older brother accepted the reply as encouragement for more and applied their touches with a firmer rhythm.

Sam gasped and yelped moving and writhing on the motel bed, legs tense and trembling as he was forced to keep them wide open for John to play with his cock and balls.

His toes began to curl, as Dean curled his fingers again and probed, brushing over his prostate.

"Fuck, oh fuck," Sam gasped, squeezing his eyes shut and bracing himself further against the floor.

He wanted to hammer his dick right through as he was hard and desperate, and John's handling of him only made his cock throb more. "Fuck Daddy please."

"Cum when you want boy, nobody is stopping you," John informed him.

"Ohmyfuckinggod," Sam groaned, Dean quickening his pace to really grind and fuck his ass with his fingers.

John dragged the orgasm from his cock with deft fingers teasing his balls into emptying. "Fuck, fuck Daddy I'm cumming, I'm cumming."

Sam ground his hips down, jerking as Dean's fingers fucked him through his orgasm.

John held his cock firm to feel it spasm as he emptied his balls against the bed, sticky cream dripping down onto the sheets.

There was a pause and then slick fingers probed at his ass again.

Sam startled in surprise, unable to move and turned with a frown to see his dad with greased fingers probing his hole.

"Sir?" he asked but John ran his free hand over his ass and pinched it quickly.

"Lay still and relax," John told him. "Are you a greedy boy Sammy?"

"Yes Sir," Sam replied honestly.

"Then let Daddy satisfy that greed like I know how," John retorted, easing a finger into his already gently loosed hole from Dean's touch.

"But Daddy," Sam groaned, huffing into the pillow as John's finger breached him easily and slid deep.

"But what son?" John asked him, moving his finger in and out.

"I already-," Sam started, whimpering as John's finger crooked and dragged slowly back out before spearing in again.

"You've already cum, yes son," John finished for him. "But you're a greedy boy, you've just admitted to me. I've tried to teach you about self - discipline and you don't learn your lesson. So, lets just satisfy that greedy lust instead hmm. Perhaps after tonight you'll learn not to be such a little slut when it comes to your pleasures."

John slipped in two fingers as he spoke, feeling Sam tense a little before relaxing into the touch.

Sam let out a soft gasp, moving slightly against the sheets.

"I'm going to keep going until you cum again," John informed him sternly. "And when you're close you're going to tell me like the good slut boy that you are, aren't you son?"

Sam whimpered as his father's fingers scissored within him, stretching his hole further.

As they worked him, spearing in and out John's other hand landed sharp on his ass, making his hips jerk and he ground back against his fingers with a gasp.

"Answer me Sammy boy," John demanded.

"Yes," Sam winced, answering with a gasping breath.

"Yes what?" John questioned, fingers sliding deep and twisting, spanking him hard again.

"Yes Daddy," Sam groaned, hugging the pillow tighter.

"What are you Sammy?" Joe teased, hand massaging into his stinging ass cheek with a firm grasp.

"Your boy Daddy," Sam replied, feeling his post pleasure dissolving into need again as John's fingers teased his body relentlessly. "Your greedy little slut boy."

Despite himself he felt his cock twitching, caught between his body and the sheets.

He started to move, pushing his sensitive cock against the mattress and then slightly back against John's fingers, beginning to fuck himself.

"Fuck, such a greedy slut," John said in response, "Look at you fucking yourself on my fingers. That's it boy, work for it."

Sam lifted onto his elbows slightly spreading his legs wider and grinding back, John's hand a steady presence as he lost himself in the pleasure.

Sensitive and spent but yes, greedy for it like John and Dean - like his dad and big brother - knew he was.

With the thought of Dean watching what was happening, Sam dropped his head and sucked in a deep breath, letting out a groan.

Dean's fingers had already fucked him thoroughly and now John's equally dragged him to the brink.

The pleasure didn't pool as quickly in his gut and his breathing was labored as he pushed for it, reaching like he was stretching out with fingertips to grasp the edge of pleasure.

His balls and cock twitched and protested as he fucked himself on John's thick calloused fingers, all moans and cries of pleasure against the sheets and his Daddy urging him on.

"Fuck Daddy, so close," Sam gasped out between breaths.

John kept his fingers moving and crooked them again, dragging them against his sensitive insides.

"Daddy, fuck, ohmygod, Daddy," Sam groaned, knuckles white as he grasped the sheets. "Daddy I'm close, please, please."

"Ask me like a good little boy," John teased unrelenting in teaching this lesson to his greedy boy.

"Please, Daddy, let me cum, please Sir," Sam begged, this pleasure was going to be dark, it made him afraid to come so soon after the last time but he wanted to experience it also.

Wanted his Daddy to demand it from his body. "Daddy please let your poor little slut boy cum."

"Such a slut," John murmured lovingly, pressing his face to Sam's ass a minute and biting the flesh before he pushed up. "Come on boy, cum for your Daddy again."

"ThankyouDaddythankyou, oh fuck" Sam managed to stutter out before he touched that edge, was propelled over it suddenly, cock spasming, balls tight as they released, expelling a little cream into the sheets.

John's fingers remained in him as he shuddered, writhed and fell to the mattress breathless and trembling.


	5. Chapter 5

Day One Part Five

Sitting by Sammy's side on the bed dancing his fingers across his brother's naked tummy relentlessly making Sam breathlessly laugh Dean grinned at him mockingly.

Dragging his fingers up his chest to his nipples circling, tickling, teasing until they were hard again, he then continued the torture up to his brother's ticklish armpits.

Watching his father circle his brother's cock torturously up and down making him hard again Dean brought up the memory while tickling Sammy's armpits slowly.

"Hey dad you remember that time when we were watching that movie Sam was laying between us, his pants and underwear down at his ankles, making him helpless and unable to move and we tickled him slowly for hours, just tied him up between us and made him take it and we used that cock ring and butt plug maybe we should do that to him again. Set the timer and see how many hours he can take it."

John grinned wickedly nodding and replied in a low voice, "Yeah I think we can do that what do you say Sammy? How long can you take this? Let's see."

Dean answered, "I'll check to see what's on TV real quick here," while continuing the drag of the soft pad of his finger up and down and in and around Sammy's armpit.

With Sam tied to the bed and Dean with one hand softly tickling his armpit with his dad stroking him, John moved to lay by Sam on the bed on the opposite side.

Eyeing the ongoing movie playing they were more intently focused on Sam's sexual torture, and the sounds he made as they played with his body.

Then Dean had a wicked idea as he reached over to grab one of their cloths lying around and came back to the bed, lying by Sammy as he tied it around Sammy's eyes.

At least this way he could feel but not see what they were doing to him this time.

John got up for a moment walking over to the dresser, and took out the custom made, hand crafted sexual toys.

Handing it to his eldest as he once again laid by the naked vulnerable body of his youngest, he watched as Dean carefully placed his brother's cock inside and locked the small padlock.

Now Sam's cock was long, and unable to get any friction at all.

And while John was busy once again tickling Sammy agonizingly slowly, Dean began to lightly graze his fingers up and down Sam's cock making him shiver.

He wrapped his hand fully around the thick cock and began stroking gently, using the precum for lubrication.

Sammy moaned and struggled bringing a smirk to both of their faces, as Dean watched, and listened carefully taking note of every moan, gasp, and whine.

Once they had brought him near the edge, Dean quickly removed his hand.

They watched in amusement as Sam attempted to hump the air to gain further friction, but Dean said darkly with a chuckle, "You will learn to control yourself Sammy boy, your orgasms belong to us right now, just take it. Now you will cum when we say you can. We still have quite a while to go. Just take it for us."

Despite their attempts to warm it, the lube is still a little chilly when Dean's finger circles his entrance.

It's a slow slide, a deliberate tease, and he tries not to squirm with impatience.

"Please." Sam begs and pleads. "More."

John and Dean seem to ignore him, as John continues softly slowly tickling his upper body as Dean kept a slow, steady pace of circles, occasionally poking and prodding at the puckered flesh, never quite entering him.

Sammy's dick tries to get hard but with the cock cage it kept deflating as a pool of pre-cum has already gathered underneath it.

Dean scoops some up and rubs it in with the copious amount of lube.

When Dean pushes his middle finger in up to the first knuckle, Sam isn't expecting it.

"Fuck, Dean!" Sam breathes, yet again fighting the urge to move, to push back on that finger and make it go deeper.

He knows that will just make his big brother pull away and tease it out of him that much longer.

After a few short thrusts, Dean starts slowly finger fucking him in earnest, two fingers moving at a steady very slow and agonizing pace, and then he's not fucking him at all, just tap, tap tapping on his prostate.

John smirks wickedly watching his eldest son teasing and dragging it out of their youngest this way.

Sam's whole body attempts to jerk forward nearly breaking the restraints.

"Dean, Dean…. It's too much I can't…."

Their father slowly twirls his fingers relentlessly over his son's underarms responding seductively, "You can and you will."

Meanwhile Dean continues his little agonizing tapping assault on his little brother's prostate, and teases his fingers in and out slowly back and forth, and then tapping again.

Each little stroke, each tiny poke shoots sparks up his spine.

"Please, I'm gonna cum, I wanna come, please Dean," he begs.

The fingers inside him go still, and the other hand clamps down on the base of his dick.

"Nope, you're not cumming until we give you permission which will be maybe another few hours so just see how long you can take it Sammy."

"Oh god." Sam whispers, raw and needy.

As Dean's fingers begin fucking him again their father twists and plucks at Sammy's nipples.

They've always been extremely sensitive and his back arches off the bed.

John reaches for a toy he and Dean had bought that Dean had grown addicted to using on Sam.

They had bought a small egg vibrator and a butt plug to tease Sammy with.

Dean glanced up grinning as John handed it to him.

He slowly but surely slid the egg up inside Sam, feeling his brother's hips twitch in response.

Waiting a few moments his father handed him the plug next.

Dean teased dragging it out as he slid the butt plug very slowly up and down Sam's anal region just slowly teasing and taunting him by pushing just an inch or two then withdrawing.

After ten more agonizing minutes of Sam moaning, John continued tickling his son, while Dean worked the plug up into his ass.

Dean allowed Sam room to lie on his back to rest against his chest thrusting two slick fingers in and out of Sam's little pink hole.

He's tender with his pleasure touch, pushing slowly and smoothly into Sam's ass and gently stretching the silky warm rim.

Dean loves the feeling of Sam's hole clinging to his fingers, the flesh nice and snug gripping and squeezing him while Sam's body becomes unwoven with pleasure.

Dean works him close to the edge and Sam moans, so sweet and hot, head thrown back and beautiful neck exposed.

Dean kisses his throat devotedly as he curls his fingers and trusts them steadily, and he listens, as Sam's breath grows rougher as the pleasure rises higher.

Dean's finger slides deeper and curls perfectly, stroking over his little brother's sweet spot and Sam's body surges with heat and pleasurably sparks.

"That good, baby boy?" Dean asks kindly, curling his fingers softly and slowly, petting Sam's sweet spot.

His little brother whines and his cock twitches, and Dean plunges his fingers in and out steadily, taking Sam apart with the perfect touch as Sammy's little twitching hole flutters, around his fingers.

Dean is loving and tender with his touch, no roughness, but he's ruthless in assaulting Sam's prostate and he rubs over it relentlessly until Sammy's little hips begin bucking frantically and he is babbling, "I'm gonna cum, Dean. I'm going to cum."

At this Dean squeezes and twists Sam's cock to hold off his brother's orgasm denying him even longer.

John smirks and says, "You look so beautiful, so perfect, like this don't deny it, wrecked and on edge by Dean's hand."

Sam moans at his father's words and Dean smirks as he taunted his little brother, "So tight and hot little brother, gonna shove this new toy so far up your ass that you'll be seeing stars rather than whatever it is that you are now. Then I'm going to turn it on and we are going to watch you fuck yourself on it and you'll want to beg us to let you orgasm but uh-huh that's not happening until you're sweating, needy, begging and wrecked for us."

Continuing pushing in the egg a bit more Dean murmurs softly in the tone that he knew was pure sex and lust and the one that always got Sam wet for him, "Did we mention this thing vibrates Sammy? These little bumps all over it move too, and they're going to move in you as you lay here because if you are a bad boy we won't let you move at all and it's just gonna be this thing hitting your prostate all night long."

With a soft torturous laugh he flicked the switch to the lowest setting possible and lay there watching with amusement with his father.

It took Sam all of five seconds to feel the effects of the vibrating toy in his ass and he jerked and gasped again as the device hit that sweet spot since Dean had made certain to angle it so every time his brother moved it would find that one spot that made Sam crazy.

Sam began to slightly thrust his hips back and forth to feel the vibrating toy move in him and as a small beep was heard he felt those nubs begin to roll and move in various directions inside him as they rubbed and massaged the inner walls while the tip just barely grazed his prostate with every thrust.

Dean's green eyes dropped to watch in fond amusement the way Sam's dick with the cock cage seemed to jump every time the device brushed over his prostate and how it was leaking a steady stream of precum now.

Gently tickling his brother's tummy slowly, tauntingly back and forth as his father stroked his brother's feet relentlessly, they grinned.

Using his other hand Dean dragged a finger up and down his brother's trapped cock teasing him.

He reached for the end of the butt plug and began pulling out and re-angling it, and pushing it back in again to drive him crazy.

After about an hour Dean slowly pulled out the plug and the egg but kept it on to feel the nubs continuously torturing his brother's prostate.

Finally after the egg was released Sam gasped for breath and Dean and his father chuckled, cleaning him up.


End file.
